Succinonitrile

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.

Succinonitrile
Names
Preferred IUPAC name
Butanedinitrile
Other names
  • Deprelin
  • Dicyanoethane
  • Ethylene cyanide
Identifiers
3D model (JSmol)
1098380
ChemSpider
ECHA InfoCard 100.003.441
EC Number
  • 203-783-9
MeSH succinonitrile
RTECS number
  • WN3850000
UNII
  • InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 Y
    Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N Y
  • N#CCCC#N
Properties
C4H4N2
Molar mass 80.090 g·mol−1
Appearance Colorless, waxy crystals
Odor odorless
Density 985 mg mL−1
Melting point 58 °C (136 °F; 331 K)
Boiling point 266.1 °C; 510.9 °F; 539.2 K
130 g L−1
Vapor pressure 300 Pa (at 100 °C)
Thermochemistry
145.60 J K−1 mol−1
191.59 J K−1 mol−1
139.3–140.4 kJ mol−1
−2.2848–−2.2860 MJ mol−1
Hazards
GHS labelling:
Warning
H302, H315, H319, H335
P261, P305+P351+P338
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
450 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none
REL (Recommended)
 TWA 6 ppm (20 mg/m3)
IDLH (Immediate danger)
 N.D.
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):

CH2=CHCN + HCN → NCCH2CH2CN

Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane).

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